Viru Gate Old Tallinn is actually two adjacent walled towns, the lower town (Vanalinn), which was home to the merchant class, and the upper town (Toompea) home to the ruling class. Viru Gate marks the entrance to Vanalinn. As you walk through Viru Gate your are immediately transported back in time to the medieval era. The ancient houses and narrow cobblestone streets date back to the 15th and 16th centuries, and most buildings are original, without much restoration. Viru street, Tallinn’s main shopping area, starts just beyond the gate. Hand made Estonian jumpers are a favorite souvenir.

Town Square Town Square, the center of Vanalinn, is a beautiful open space surrounded by fine old buildings. To one side of the square lies the 13th century Town Hall - a climb up its tower reveals beautiful views all around. On the other side sits a charming 15th century pharmacy, Europe’s oldest.

Russian Cathedral From the town square, if you walk up Luhike Jalg (Short Leg) you’ll reach Upper town or Toompea. In front of you stands the impressive Russian Cathedral (or Alexander Nevski Cathedral), built over the grave of an Estonian hero. Though the building has connotations of Russian imperialism for many of the Estonian population.

Toomkirk Past the Russian Catheral lies the Toomkirk, or Dome Church. This simple building was originally constructed in the 13th century by the Danes, but was reconstructed in the 17th century after a fire. The interior walls of the church are decorated with many coats of arms, each belonging to a wealthy merchant family. After you leave be sure to stop at the nearby Patkul and Kohtuotsa viewpoints for spectacular views over the medieval town.

Great Guild Hall From Toompea take the Pikk Jalg (Long Leg) down the hill back into Vanalinn. At the bottom of the street sits the Great Guild Hall, once the powerhouse of Vanalinn, as the meeting point for married merchants. (Unmarried men belonged to the lower order Brotherhood of the Blackheads). Today the building houses the History Museum of Estonia. Across the street from the Hall you’ll find the well-loved Maiasmokk coffee shop, which opened in 1864. Drop in for a steaming hot coffee, with a delicious slice of cake.